CN1123268A - Process for the treatment of halogenated hydrocarbons - Google Patents

Process for the treatment of halogenated hydrocarbons Download PDF

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Publication number
CN1123268A
CN1123268A CN94118716.0A CN94118716A CN1123268A CN 1123268 A CN1123268 A CN 1123268A CN 94118716 A CN94118716 A CN 94118716A CN 1123268 A CN1123268 A CN 1123268A
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China
Prior art keywords
hydrogenation
hydrogen
materials flow
hydrogen halide
halogenation
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CN94118716.0A
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Chinese (zh)
Inventor
E·L·德里赫
C·L·普雷拉
B·博海莫尔
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Dow Chemical Co
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Dow Chemical Co
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Priority to EP94308591A priority Critical patent/EP0643123A3/en
Priority to CN94118716.0A priority patent/CN1123268A/en
Publication of CN1123268A publication Critical patent/CN1123268A/en
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a treatment method for converting organic waste stock flow containing halogenated compound to produce hydrogenated organic compound and recovering the obtained halogen hydride as anhydrous product stock flow.

Description

The treatment process of halon
The present invention relates to by the organic materials flow production of halogenation hydrogenated hydrocarbons product and anhydrous hydrogen halide materials flow.
People contain the organic materials flow of halon and with the organic compound of producing hydrogenation and the technology of hydrogen halide materials flow growing demand are arranged handling.Preferred hydrogen halide materials flow is anhydrous, can reduce to the cost of building processing factory minimum because consider from metallurgical aspect like this.
Along with in the environmental protection processing and recirculation being contained the attention that halogenation compound organic waste materials flows, people are growing with the demand of improving one's methods of producing hydrogenation organic compound and hydrogen halide to transforming organic waste materials stream.For example disposing or recirculation when the organic waste materials of potential hazard being arranged on to environment, in the whole proposal of dealing with problems, an important step is to produce to help the final organic materials flow of dissolved again to produce the product materials flow of disposing with acceptable manner in the environmental protection subsequently.
The method of attractive processing organic waste materials stream is a hydrogenation method in a kind of environmental protection.Therefore those skilled in the art are devoted to find to transform easy row and the economic method that the organic waste materials stream that contains the halogenation compound becomes hydrogenated organic compound and reclaims the hydrogen halide of following production always.At United States Patent (USP) 4,923,590 (people such as kalnes) disclose a kind of method and have wherein contacted with wash water solution from the effluent of hydroconversion reaction zone.In an embodiment preferred, this patent points out that when the charging that is added to hydroconversion reaction zone contains halogenated compound wash water solution preferably contains a kind of basic cpd with neutralizing acid.
Yet when hydrogen halide reclaimed with Aquo System, the requirement on the metallurgy became an essential economically problem of considering.Therefore special recently hydrogen halide of wishing to reclaim gained with anhydrous process.
The invention provides that organic waste materials materials flow that a kind of conversion contains the halogenation compound becomes the organic compound of hydrogenation and with the hydrogen halide of gained as improving one's methods that the anhydrous product materials flow is reclaimed.
One embodiment of the invention can be characterized by a kind of handle the organic materials flow of halogenation after with the hydrogenation of producing halogen content and having reduced hydrocarbon flow and contain the method for the anhydrous materials flow of hydrogen halide, this method comprises the following steps: that (a) is under hydroconversion condition, in hydroconversion reaction zone with the organic materials flow of halogenation, hydrogen rich gas attitude recycle stream with contain recycle stream that the unreacted halogenated organic closes and contact with the hydrogen richness that improves the organic materials flow of described halogenation with hydrogenation catalyst and prepare hydrogen halide whereby; (b) condensation at least a portion from the effluent of hydroconversion reaction zone with preparation hydrogen rich gas attitude cycling stream with the hydrocarbon compound after containing hydrogenation and the liquid stream of hydrogen halide; (c) liquid stream that will contain hydrocarbon compound behind the hydrogenation and hydrogen halide separates the hydrocarbon compound after containing the anhydrous materials flow of hydrogen halide and contain hydrogenation with preparation and the materials flow of unreacted halogenated organic compounds; (d) materials flow that will contain hydrocarbon compound behind the hydrogenation and unreacted halogenated organic compounds separates the hydrocarbon flow after containing the cycle stock of unreacted halogenated organic compounds and reduced the hydrogenation of halogen content with preparation.
Other embodiment of the present invention comprises the details such as preferred raw material, hydrogenation catalyst and operational condition, and all these details are all open in following discussion all respects of the present invention.
Accompanying drawing is the simplification technical process functional diagram of the preferred embodiment of the invention.
The invention provides a kind of transform the halogenation hydrocarbon flow with produce the halogen content the hydrogenation hydrocarbon flow and contain the improved integral method of the anhydrous material stream of hydrogen halides. People be to processing the technology of halogenated hydrocarbon compound, particularly do not use or are that the material that uses expensive construction processes factory is down to the demand of method for the treatment of process of minimum economy is growing at least reclaiming the anhydrous material stream of hydrogen halides and providing whereby a kind of.
A large amount of halogenated organic compounds, be unsaturated or saturated all be the suitable raw material material stream of the inventive method. The example that is fit to flow with the organic material that contains the halogenation organic compound that method of the present invention is processed is dielectric, hydraulic oil, heat transmission liquid, with the ravine lubricating oil of crossing, the lubricated cutting oil of using, spent solvent, halogenated hydrocarbon is paid product, the oil that Polychlorinated biphenyls (PCB) pollutes, the halogenation waste material, petrochemical industry is paid product and other halogenated hydrocarbon industrial waste. Usually under specific occasion, there is the organic material stream of two or more halogenation to need further to process. What halogenated organic closed can be hydrogeneous, is called hydrocarbon compound under this occasion.
According to the present invention, the halogenation Organic Ingredients preferably contains less than the water of 50ppm (weight) and (in some cases) product water precursor. The example that produces the water precursor is the compound of oxidation, and these compounds are at the compound and the water that are in the presence of the required catalyst after being converted to hydrogenation under the hydroconversion condition. The term " the anhydrous material stream that contains hydrogen halides " that is used for this paper means water content less than the material stream of 50ppm (weight)
Preferred raw material comprises the separation column bottoms of producing chlorallylene, produces the separation column bottoms in the Ethylene Dichloride, produces the separation column bottoms in trieline or the tetrachloroethylene, that exhausted contains polychlorobiphenyl or benzene halide insulating liquid, spent solvent is from the tower bottom distillate of producing the Epicholorohydrin purification column, tetracol phenixin, 1,1,1-trichloroethane, halohydrin, halogenated ethers, cfc or its mixture.
The halogenated organic compounds that can be used as raw material of the present invention can be chloride, bromine, fluorine or iodine.The preferred chloride or fluorine of halogen compound.
According to the present invention, the raw material that will contain the halogenation organic compound and hydrogen rich gas attitude recycle stream and the recycle stream that contains unreacted halogenated hydrocarbon compound mix to guide to and contain hydrogenation catalyst and also maintained catalytic hydrodesulfurizationzone zone under the hydroconversion condition.This catalytic hydrodesulfurizationzone zone can contain fixed bed, ebullated bed or fluidized-bed.This reaction zone preferably maintains can be under the condition of introducing halogenated organic compounds dehalogenation wherein.This catalytic hydrodesulfurizationzone zone preferably maintains normal pressure to 2000psig (13.8Mpa, gauge pressure), is preferably in 100psig (0.7Mpa, gauge pressure) under 1800psig (12.4Mpa, gauge pressure).It is that 122F (50 ℃) suits under 850 °F (454 ℃) that this class is reflected at the maximum catalyst bed temperature, and therefore the concentration of selecting such temperature range to reduce halogenated organic compounds in the mixing raw material materials flow to carry out desirable dehalogenation to transform also improve the hydrogen richness of this materials flow.Expect that required hydrocracking comprises, for example, dehalogenation and hydrocracking.Preferred operational condition comprises that the liquid hourly space velocity degree is at 0.05hr -1To 20hr -1In the scope and hydrogen circulation rates be from 200 standard cubic feet per barrels (SCFB) (35 standard m 3/ m 3) to 100000SCFB (18,000 standard m 3/ m 3), be preferably 200SCFB to 50000SCFB (9,000 standard m 3/ m 3).
The term " hydrogenation " that is used for the present invention means some reactions and borrows these reaction organic reactants to improve hydrogen richness, and no matter the raising of hydrogen richness is that the saturation by alkene, saturation, desulfurization, denitrogenation or the dehalogenation of diene are finished.
According to the present invention, will from containing of hydrogenation zone at least a hydrogen halide compound the hydrocarbon effluent guide in vapour one liquid/gas separator with the hydrocarbon compound after obtaining hydrogen rich gas attitude recycle stream and containing hydrogenation and the liquid stream of hydrogen halide.The liquid stream that contains hydrocarbon compound behind the hydrogenation and hydrogen halide of gained is separated the hydrocarbon compound after containing the anhydrous materials flow of hydrogen halide and contain hydrogenation with preparation and the liquid stream of unreacted organic compound.Then the liquid stream of gained is separated with preparation and contain hydrocarbon flow behind the hydrogenation that the recycle stream (it is introduced to hydroconversion reaction zone) of unreacted halogenated organic compounds and halogen content reduced.According to the present invention, the hydrogen halide compound is reclaimed as the anhydrous product materials flow.This makes that the subsequent recovery of required valuable hydrogen halide compound is more convenient with use.
Place the preferred catalyst complex in above-mentioned hydrogen district to be characterized by and contain metal component, this component and suitable synthetic or natural infusibility solid support material bonded catalyzer with hydrogenation activity.The accurate method of forming and prepare solid support material is not critical to the invention.Preferred solid support material is an aluminum oxide, silicon oxide, carbon and composition thereof.The suitable metal component that hydrogenation activity is arranged is to be selected from E.H.Sargent and company, the VIB of 1964 the periodic table of elements and VIII family metal.Like this, catalytic complex can comprise a kind of molybdenum that is selected from, tungsten, chromium, iron, cobalt, nickel, platinum, palladium, iridium, osmium, ruthenium, the metal of rhodium and composition thereof.Catalytically-active metals component or a plurality of component concentrations depend primarily on the physics and/or the chemical property of concrete metal and concrete hydrocarbon feed.For example the common amount of group vib metal component is 1%-20% (weight), the amount of iron family metal is 0.2%-10% (weight), and the metal of VIII family preferably to measure be 0.1-5% (weight), all these amounts all are present in the catalytic complex with element form by these components to be calculated.Further expectation hydrogenation catalyst mixture can comprise one or more following components: cerium, francium, lithium, potassium, rubidium, sodium, copper, gold, silver, cadmium, mercury and zinc.Preferred hydrogenation catalyst comprises aluminum oxide and palladium.
As mentioned above, preferably the hydrocarbon effluent behind the hydrogenation that will obtain from hydroconversion reaction zone separates in the disengaging zone to obtain hydrogen rich gas mutually and liquid hydrocarbon stream, the disengaging zone maintains the temperature of the pressure identical with hydroconversion reaction zone and-70 (57 ℃) to 40 (4.4 ℃), the result, liquid hydrocarbon stream contains dissolved hydrogen, and dissolved hydrogen halide and lower molecular weight are generally gasiform hydrocarbon (if present).According to the present invention, behind the hydrogenation behind the Halogen liquid phase of hydrogen by separating for example stripping, flash distillation or fractionation with preparation anhydrous hydrogen halide materials flow.After making hydrogen halide and from this technical process, removing, the separate hydrocarbons materials flow is to prepare hydrocarbon flow that mainly contains the hydrocarbon compound behind the hydrogenation and the hydrocarbon flow that mainly contains halogenated organic compound, if desired, the materials flow that mainly contains halogenated organic compound is recycled to hydroconversion zone.This class is separated can any usual manner such as stripping, and flash distillation or fractionation are carried out.
In the accompanying drawings, method of the present invention is to illustrate with the simplification process block diagram, and wherein such as reaction zone and moisture eliminator sum, pump, instrument are not crucial with similar equipment because to understanding related technology, thereby are left out.Using this class auxiliary facility is well known to a person skilled in the art.
Referring now to accompanying drawing, the halogenation organic raw material that contains the halogenation organic compound through pipeline 1 introduce and with the hydrogen rich gas of introducing through pipeline 7 that will be further described below recycle stream contact mutually.To contain the halogenation organic raw material materials flow of halogenation organic compound, rich hydrogen recycle stream and be incorporated into hydroconversion reaction zone 2 by the organic recycle stream of unconverted halogenation that below will describe that pipeline 14 provides.Through pipeline 3 the organic materials flow of the hydrogenation of gained is removed and in heat exchanger 4 coolings, is incorporated in the vapour liquid separator 6 through pipeline 5 from hydroconversion reaction zone 2.The materials flow of hydrogen rich gas phase is removed from vapour liquid separator 6 and by mode recirculation described above through pipeline 6.Because hydrogen has loss in technology be that hydrogen partial is dissolved in the liquid hydrocarbon of discharge and consumes hydrogen in hydrogenation reaction, must flow mutually by the hydrogen make hydrogen rich gas of some external sources such as catalyst regeneration units or hydrogen factory.Where the hydrogen that replenishes can in officely just and on the suitable position (not shown) be introduced.The liquid hydrogenated hydrocarbons materials flow that will contain hydrogen and hydrogen halide solution is removed from vapour liquid separator 6 and is incorporated in the fractionation zone 9 through pipeline 8.The product materials flow that contains hydrogen halide is removed and is reclaimed from fractionation zone 9 through pipeline 10.Distillable hydrogenated hydrocarbons materials flow is removed and is incorporated into the fractionation zone 12 from fractionation zone 9 through pipeline 11.The product materials flow that contains the reduction of hydrocarbon compound and halogen concentration is removed and is reclaimed from fractionation zone 12 through pipeline 13.The liquid stream that contains unconverted halogenated organic compounds is recycled in the hydroconversion reaction zone 2 through pipeline 14.
The following example is intended to further specify method of the present invention and shows use this method by the organic materials flow production of halogenation hydrogenated hydrocarbons materials flow with contain the benefit of the anhydrous materials flow of hydrogen halide.Embodiment
The halogenation organic raw material that will have a listed characteristic of table 1 is added to the speed of 47.8mol/hr and is equipped with in the hydroconversion reaction zone that is loaded in the palladium catalyst on the aluminum oxide.Hydrogenation reaction is carried out under hydroconversion condition.Hydroconversion condition comprises that temperature is 176 °F (80 ℃); Pressure is that 750psig (5.2Mpa, gauge pressure) and hydrogen circulation rates are 20000 SCFB (3,600 standard m 3/ m 3)
Table 1
Halogenation organic raw material performance
Form Weight percentage
Chlorination propane ????91.1
Unsaturated propane ????4.7
Other ????4.2
The hydrocarbon flow (below will describe) that contains unconverted raw material is added to hydroconversion reaction zone with the amount of 30mol/hr.
The effluent that derives from hydroconversion reaction zone is cooled to-15 ℃ and be incorporated in vapour-liquid/gas separator.The materials flow of hydrogen rich gas phase is removed from vapour-liquid/gas separator, and it contains the hydrogen of 2000mol/hr, the hydrogenchloride of 850mol/hr and the chlorinated hydrocarbon of 70mol/hr.Liquid stream is removed from vapour-liquid/gas separator, and its amount comprises 50mol/hr propane, 60mol/hr hydrogenchloride and 25mol/hr chlorinated hydrocarbon for 140mol/hr.This liquid stream fractionation is contained the hydrogenchloride product of 60mol/hr with preparation, contain the propane product materials flow of 48mol/hr propane and contain the liquid recycle stream of 30mol/hr chlorinated hydrocarbon.
Above-mentioned description, drawings and Examples have clearly illustrated the advantage of the inventive method and have used the benefit of this method.

Claims (8)

1. method of handling the hydrocarbon flow of the hydrogenation that halogenation organic materials flow reduced with the preparation content of halogen and containing the anhydrous materials flow of hydrogen halide, this method comprises the following steps:
(a) under hydroconversion condition, in hydroconversion reaction zone with the organic materials flow of halogenation, hydrogen rich gas attitude recycle stream with contain recycle stream that the unreacted halogenated organic closes and contact with the hydrogen richness that improves the organic materials flow of described halogenation with hydrogenation catalyst and prepare hydrogen halide whereby;
(b) condensation at least a portion from the effluent of hydroconversion reaction zone with preparation hydrogen rich gas attitude cycling stream with the hydrocarbon compound after containing hydrogenation and the liquid stream of hydrogen halide;
(c) liquid stream that will contain hydrocarbon compound behind the hydrogenation and hydrogen halide separates the hydrocarbon compound after containing the anhydrous materials flow of hydrogen halide and contain hydrogenation with preparation and the materials flow of unreacted halogenated organic compounds; With
(d) materials flow that will contain hydrocarbon compound behind the hydrogenation and unreacted halogenated organic compounds separates the hydrocarbon flow after containing the recycle stream of unreacted halogenated organic compounds and reduced the hydrogenation of halogen content with preparation.
2. the process of claim 1 wherein that the organic materials flow of described halogenation comprises the separation column substrate of producing in the chlorallylene, produces the separation column bottoms in the Ethylene Dichloride, produce the separation column bottoms in trieline or the tetrachloroethylene, exhausted contains the insulating liquid of polychlorobiphenyl, benzene halide, spent solvent is from the tower bottom distillate of producing the Epicholorohydrin purification column, tetracol phenixin, 1,1,1-trichloroethane, halohydrin, halogenated ethers, cfc or its mixture.
3. the process of claim 1 wherein that the organic materials flow of described halogenation contains water or the product medusa less than 50ppm (weight).
4. the process of claim 1 wherein that the described anhydrous materials flow that contains hydrogen halide contains the water less than 50ppm (weight).
5. the process of claim 1 wherein that described hydrogenation reaction still operates under following condition: pressure is (gauge pressure) from the normal pressure to 13.8MPa, the maximum catalyst temperature from 50 ℃ to 454 ℃ and hydrogen circulation rates from 35 standard m 3/ m 3To 9,000 standard m 3/ m 3
6. the process of claim 1 wherein that described hydrogenation catalyst comprises refractory inorganic oxide and at least a metallic compound that hydrogenation activity is arranged.
7. the method for claim 6, wherein said metallic compound is selected from the metal of periodictable VIB and VIII family.
8. the process of claim 1 wherein that described hydrogen halide is a hydrogenchloride, hydrogen bromide, hydrogen halide or hydrogen iodide.
CN94118716.0A 1994-11-21 1994-11-21 Process for the treatment of halogenated hydrocarbons Pending CN1123268A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94308591A EP0643123A3 (en) 1994-11-21 1994-11-21 Process for the treatment of halogenated hydrocarbons.
CN94118716.0A CN1123268A (en) 1994-11-21 1994-11-21 Process for the treatment of halogenated hydrocarbons

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Application Number Priority Date Filing Date Title
EP94308591A EP0643123A3 (en) 1994-11-21 1994-11-21 Process for the treatment of halogenated hydrocarbons.
CN94118716.0A CN1123268A (en) 1994-11-21 1994-11-21 Process for the treatment of halogenated hydrocarbons

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FR2780300B1 (en) * 1998-06-25 2000-11-10 Rhodia Chimie Sa PROCESS FOR TREATING GASES OR LIQUIDS FROM CATALYTIC REFORMING

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DE3623430A1 (en) * 1986-07-11 1988-01-28 Veba Oel Entwicklungs Gmbh METHOD FOR HYDROGENATING TREATMENT WITH CHLORBIPHENYLENE AND THE LIKE CONTAMINATED MINERAL OILS
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EP0643123A2 (en) 1995-03-15
EP0643123A3 (en) 1995-08-23

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